Ask a Dude: Should I Ask If He Likes Me Back?

So basically I’ve never been in a relationship or gone on a date with a guy. Over the years, I’ve liked a lot of my friends but I’ve always been too afraid to make the first move because I feel like they don’t like me in that way. A lot of the time, though, other people can tell that I like the guy but I never bring it up to him directly, and I just always think to myself “well if he liked you, he’d ask you out, it has to be obvious that I like him.”

I’ve talked to a few of the guys later on when we hadn’t talked to each other in a while, and in each of the cases the guy admitted to liking me at the same time I had liked them. I’m just so confused now because I really like this new guy, but I honestly can’t tell if he feels the same way. I just don’t know how to bring it up to him without seeming obsessive or making things super awkward between us, but at the same time I feel like I’ll regret it down the line if I find out later that he had feelings for me the entire time.

I’m just getting such mixed messages because he always tells me how much he likes talking to me and he compliments me a lot…but at the same time I can’t tell if that’s just pure friendship or if he might feel something more too. And I just really love him so much as a person that I don’t want to ruin our friendship over this…but it’s bothering me not knowing for sure if he likes me or not!

How do I know for sure if he really is just not that into me?

-Completely Confused

Dear Completely Confused,

There’s nothing that halts the course of happiness more completely than fear we can’t set aside. Unfortunately, it sounds like your fear of rejection, and thus of getting hurt, is what’s keeping you in the “not knowing” circle of Hell. Well, there’s only so many ways to skin this cat. They all involve you being active.

We all have patterns. We all have defense mechanisms. We all have habitual behaviors that we think are the best we can come up with to attain pleasure, happiness, joy, etc. However, we also all have breaking points. This is where the pain we create by these behaviors, mechanisms and patterns is greater than the pleasure they provide. That’s when we’re ripe for a change. Sounds to me like you’re reaching that breaking point. Hence, you’re reaching out for help. That’s not a bad thing, that’s a good thing!

If being passive, hanging back until a guy asks you out, is causing nothing but regret and frustration, then the answer to Dr. Phil’s patented question: “How’s that workin’ for ya?” is, “like sh*t.” Time to let go of the pattern of waiting and create a new pattern of taking initiative. You’re not asking him to marry you, you’re not asking him to carry all of your emotional baggage, you’re asking if he wants to spend two hours having a couple beers or in a darkened movie theater, or on your couch watching Cowboy Be-Bop. Keep it in perspective.

Everyone’s scared of getting hurt. It’s programmed into our homo-sapien-sapien DNA. Nobody jumps in line to fall on her sword. But let’s be realistic, asking a guy out and falling on a sword, while they may sound similar, are in fact two very different types of putting yourself out there. Keep it in perspective.

Asking a guy out doesn’t banish him from your life, but does it risk awkwardness? Sure. You know what it also risks? Him saying “yes.” And if he says “no” then that doesn’t make you less worthy of dating, it just means that for one reason or another, you’re not going to go out with this guy. Still 150 million other options exist in the U.S. alone. Keep it in perspective.

Asking someone out is like any other skill, it gets easier with practice. You talk to anyone in the arts and you’ll feel better about a guy saying no to Saturday night. Those folks are in the business of constant rejection. They’re also in the business of constantly having to put themselves out there. The first time will be the hardest. But just keep it in mind that the regret of not knowing is a far more chronic pain than the sting of a rejection. The second time will be hard but you’ll have experience to draw on. Sometimes it’s easier to start by asking out someone you’re not Jonesing for. Sometimes it’s easier when it’s someone you’re just meeting and having a decent conversation with. Then, work your way up to the boys whose names you’ve been doodling hearts around all year.

The bottom line is: Yes, it’s time you started getting comfortable making the first move. Yes, it’s time you stopped letting your fear keep getting you hurt through inaction. Yes, it’s time to grow a pair and put yourself out there! Keep it in perspective, how much worse could it be than what you’re going through now? Answer: Probably none.

Always asking,

Marcus Duderelius

[Isn’t he amazeballs? Sigh, we know. Too bad he’s taken. Check out The Dude’s other insights into the male mind right here.]